1-Methylpiperazine → HCID 12521666, compound

HRID 1605914Notes

Reaction equation

HRID 1605914 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7](SC)[C:8]3[C:9](=[CH:11][S:12][CH:13]=3)[NH:10][C:4]=2[CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(O)(=O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)[C:8]3[C:9](=[CH:11][S:12][CH:13]=3)[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 12521661HCID 12521661, compound

Product 1

HCID 12521666HCID 12521666, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

A solution of 0.7 g. of 6-chloro-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine in 3.5 ml. of N-methylpiperazine is treated with 1-2 drops of glacial acetic acid and heated undr reflux for 4 days. The solution is concentrated to dryness and the residue is warmed with dilute acetic acid. The acidic solution is filtered, cooled, and made alkaline with concentrated ammonium hydroxide. The precipitate is collected, washed with water and recrystallized from acetone-petroleum ether (30°-60°C.) to give yellow crystals, m.p. 148°-149°C. (dec.).

Workup

  1. temperatureheated undr
  2. temperaturereflux for 4 days
  3. concentrationThe solution is concentrated to dryness
  4. temperaturethe residue is warmed with dilute acetic acid
  5. filtrationThe acidic solution is filtered
  6. temperaturecooled
  7. customThe precipitate is collected
  8. washwashed with water
  9. customrecrystallized from acetone-petroleum ether (30°-60°C.)
  10. customto give yellow crystals, m.p. 148°-149°C. (dec.)

Sources & evidence

ORD record
ord-c8eed91ca3e54ebc87fc2113aef564bd
Source dataset
uspto-grants-1976_04
Patent number
US03951981

Reaction notes

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